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In the title compound, [Fe(C5H5)(C20H23)], the two five-membered cyclo­penta­dienyl rings are nearly parallel, with a dihedral angle of only 3.8 (1)°. The dihedral angle between the indenyl plane and the substituted cyclo­penta­dienyl ring is 58.1 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028308/cf6450sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028308/cf6450Isup2.hkl
Contains datablock I

CCDC reference: 287496

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.044
  • wR factor = 0.121
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

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Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C10
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

A number of ferrocene derivatives substituted with an indenyl group have been structurally characterized, including 2-ferrocenyl-2-(3-indenyl)propane (Gaede, 2000), 1-(ferrocenyl)indene and 2-(ferrocenyl)indene (Plenio, 1992). As a further contribution, we report here the synthesis and crystal structure of 1-ferrocenyl-1-(1-indenyl)cyclohexane, (I).

A view of (I) is shown in Fig. 1 and selected bond lengths and angles are listed in Table 1. The dihedral angle between the indenyl plane and the substituted cyclopentadienyl ring is 58.1 (2)°. The Fe atom is η5-coordinated by both cyclopentadienyl rings, with distances ranging from 2.015 (4) (to C10) to 2.074 (3) Å (to C1). The two five-membered cyclopentadienyl rings are nearly parallel, forming a dihedral angle of only 3.8 (1)°. The cyclohexane ring has a normal chair conformation.

Experimental top

A solution of indene (1.39 ml, 12 mmol) in tetrahydrofuran (THF, 100 ml) was reacted with n-butyllithium (12 mmol) at 273 K for 2 h and then stirred at room temperature for 4 h. A solution of 6,6-pentamethylenefulvene (1.75 g, 12 mmol) in THF (20 ml) was added dropwise at 273 K with stirring. When the addition was complete, the solution was warmed to room temperature and stirring was continued overnight. Cyclopentadienyllithium (12 mmol) in THF (20 ml) was added to this reaction mixture, followed by FeCl2·1.44THF (2.78 g, 12 mmol), and the mixture was then stirred overnight. The solvent was removed under vacuum. The residue was chromatographed through a short column of Al2O3 with CH2Cl2, yielding an orange solid, which was collected and purified by chromatography on alumina to give orange crystals (yield 1.24 g, 27.07%). Calculated for C26H28Fe: C 78.54, H 6.85%; found: C 78.65, H 6.61%.

Refinement top

H atoms were placed in calculated positions, with C—H = 0.93–0.98 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omited for clarity.
1-Ferrocenyl-1-(1-indenyl)cyclohexane top
Crystal data top
[Fe(C5H5)(C20H21)]F(000) = 808
Mr = 382.31Dx = 1.341 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.232 (2) ÅCell parameters from 2652 reflections
b = 11.6546 (18) Åθ = 2.3–24.3°
c = 12.293 (2) ŵ = 0.80 mm1
β = 92.881 (3)°T = 294 K
V = 1893.4 (5) Å3Block, red
Z = 40.26 × 0.24 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3887 independent reflections
Radiation source: fine-focus sealed tube2407 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 26.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.793, Tmax = 0.866k = 146
10458 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0562P)2 + 0.5012P]
where P = (Fo2 + 2Fc2)/3
3887 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
[Fe(C5H5)(C20H21)]V = 1893.4 (5) Å3
Mr = 382.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.232 (2) ŵ = 0.80 mm1
b = 11.6546 (18) ÅT = 294 K
c = 12.293 (2) Å0.26 × 0.24 × 0.18 mm
β = 92.881 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3887 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2407 reflections with I > 2σ(I)
Tmin = 0.793, Tmax = 0.866Rint = 0.038
10458 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.01Δρmax = 0.41 e Å3
3887 reflectionsΔρmin = 0.30 e Å3
235 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.28071 (3)0.07033 (4)0.58622 (3)0.04852 (17)
C10.2795 (2)0.0327 (2)0.7237 (2)0.0409 (7)
C20.2929 (2)0.0853 (2)0.7522 (2)0.0466 (7)
H20.25070.12780.79500.056*
C30.3805 (3)0.1266 (3)0.7051 (2)0.0602 (9)
H30.40620.20070.71160.072*
C40.4227 (3)0.0356 (3)0.6460 (3)0.0633 (9)
H40.48100.03940.60690.076*
C50.3608 (2)0.0616 (3)0.6569 (3)0.0522 (8)
H50.37130.13300.62570.063*
C60.1719 (4)0.1759 (5)0.5225 (3)0.0965 (16)
H60.13210.22460.56220.116*
C70.2592 (5)0.2030 (4)0.4800 (4)0.0955 (15)
H70.29030.27440.48590.115*
C80.2951 (4)0.1150 (5)0.4287 (3)0.0968 (14)
H80.35560.11530.39340.116*
C90.2331 (5)0.0240 (4)0.4333 (3)0.0974 (17)
H90.24260.04730.40150.117*
C100.1498 (4)0.0569 (6)0.4961 (4)0.117 (2)
H100.09490.01280.51530.140*
C110.2002 (2)0.1131 (2)0.7658 (2)0.0411 (7)
C120.1038 (2)0.0461 (2)0.7892 (3)0.0488 (7)
H12A0.08170.00380.72430.059*
H12B0.11960.00930.84650.059*
C130.0170 (2)0.1222 (3)0.8235 (3)0.0627 (9)
H13A0.04230.07530.83420.075*
H13B0.03600.15950.89200.075*
C140.0084 (3)0.2126 (3)0.7372 (3)0.0734 (10)
H14A0.03560.17540.67150.088*
H14B0.06010.26350.76300.088*
C150.0836 (3)0.2823 (3)0.7107 (3)0.0675 (10)
H15A0.10450.32870.77340.081*
H15B0.06590.33370.65070.081*
C160.1712 (2)0.2064 (3)0.6801 (3)0.0561 (8)
H16A0.22980.25440.66980.067*
H16B0.15340.16920.61120.067*
C170.2476 (2)0.1731 (2)0.8710 (2)0.0439 (7)
H170.19820.22920.89480.053*
C180.3447 (3)0.2372 (3)0.8537 (3)0.0558 (8)
H180.35270.29100.79900.067*
C190.4169 (3)0.2070 (3)0.9260 (3)0.0618 (9)
H190.48230.23650.92930.074*
C200.3799 (2)0.1215 (3)0.9995 (2)0.0486 (7)
C210.2782 (2)0.0996 (2)0.9682 (2)0.0410 (7)
C220.2237 (2)0.0261 (3)1.0322 (2)0.0492 (7)
H220.15580.01141.01440.059*
C230.2710 (3)0.0250 (3)1.1223 (3)0.0612 (9)
H230.23430.07381.16540.073*
C240.3716 (3)0.0050 (3)1.1496 (3)0.0663 (9)
H240.40260.04181.20960.080*
C250.4264 (3)0.0689 (3)1.0889 (3)0.0635 (9)
H250.49410.08341.10790.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0677 (3)0.0461 (3)0.0316 (2)0.0057 (2)0.00016 (19)0.00341 (19)
C10.0480 (17)0.0434 (16)0.0310 (14)0.0034 (13)0.0016 (12)0.0037 (12)
C20.0625 (19)0.0469 (18)0.0299 (14)0.0066 (15)0.0033 (13)0.0001 (12)
C30.072 (2)0.063 (2)0.0454 (18)0.0206 (19)0.0049 (16)0.0080 (16)
C40.054 (2)0.079 (2)0.058 (2)0.0048 (18)0.0067 (16)0.0196 (19)
C50.0559 (18)0.0524 (19)0.0486 (17)0.0088 (16)0.0053 (14)0.0078 (15)
C60.109 (4)0.133 (5)0.046 (2)0.070 (4)0.007 (2)0.005 (3)
C70.165 (5)0.064 (3)0.056 (3)0.019 (3)0.015 (3)0.017 (2)
C80.143 (4)0.114 (4)0.034 (2)0.013 (4)0.009 (2)0.011 (2)
C90.175 (5)0.058 (3)0.053 (3)0.010 (3)0.046 (3)0.011 (2)
C100.086 (3)0.177 (6)0.082 (3)0.055 (4)0.049 (3)0.078 (4)
C110.0463 (17)0.0375 (15)0.0394 (15)0.0022 (13)0.0023 (12)0.0022 (12)
C120.0498 (18)0.0478 (18)0.0483 (17)0.0039 (14)0.0018 (14)0.0021 (14)
C130.050 (2)0.068 (2)0.070 (2)0.0006 (17)0.0088 (17)0.0031 (19)
C140.060 (2)0.083 (3)0.076 (3)0.020 (2)0.0076 (19)0.004 (2)
C150.078 (2)0.057 (2)0.066 (2)0.0170 (19)0.0061 (18)0.0117 (17)
C160.067 (2)0.0505 (19)0.0508 (19)0.0050 (16)0.0006 (15)0.0101 (15)
C170.0534 (17)0.0347 (15)0.0441 (16)0.0012 (13)0.0083 (13)0.0051 (13)
C180.074 (2)0.0440 (18)0.0507 (19)0.0193 (16)0.0117 (17)0.0039 (15)
C190.060 (2)0.070 (2)0.056 (2)0.0285 (18)0.0105 (17)0.0130 (17)
C200.0487 (18)0.0555 (18)0.0418 (16)0.0060 (15)0.0057 (13)0.0127 (14)
C210.0466 (17)0.0421 (16)0.0347 (15)0.0020 (13)0.0038 (12)0.0103 (12)
C220.0506 (18)0.0558 (18)0.0416 (17)0.0091 (15)0.0071 (14)0.0028 (14)
C230.078 (2)0.064 (2)0.0419 (18)0.0104 (18)0.0081 (17)0.0022 (16)
C240.080 (3)0.077 (2)0.0411 (18)0.006 (2)0.0068 (18)0.0013 (18)
C250.0541 (19)0.088 (3)0.0473 (19)0.0022 (19)0.0050 (16)0.0113 (19)
Geometric parameters (Å, º) top
Fe1—C12.074 (3)C11—C171.573 (4)
Fe1—C22.046 (3)C12—C131.528 (4)
Fe1—C32.028 (3)C12—H12A0.970
Fe1—C42.023 (3)C12—H12B0.970
Fe1—C52.037 (3)C13—C141.521 (5)
Fe1—C62.021 (4)C13—H13A0.970
Fe1—C72.035 (4)C13—H13B0.970
Fe1—C82.024 (4)C14—C151.512 (5)
Fe1—C92.026 (4)C14—H14A0.970
Fe1—C102.015 (4)C14—H14B0.970
C1—C51.426 (4)C15—C161.520 (4)
C1—C21.428 (4)C15—H15A0.970
C1—C111.517 (4)C15—H15B0.970
C2—C31.406 (4)C16—H16A0.970
C2—H20.930C16—H16B0.970
C3—C41.416 (5)C17—C211.509 (4)
C3—H30.930C17—C181.510 (4)
C4—C51.408 (4)C17—H170.980
C4—H40.930C18—C191.319 (4)
C5—H50.930C18—H180.930
C6—C71.329 (6)C19—C201.447 (4)
C6—C101.450 (7)C19—H190.930
C6—H60.930C20—C251.377 (4)
C7—C81.305 (6)C20—C211.404 (4)
C7—H70.930C21—C221.388 (4)
C8—C91.344 (7)C22—C231.380 (4)
C8—H80.930C22—H220.930
C9—C101.429 (7)C23—C241.377 (5)
C9—H90.930C23—H230.930
C10—H100.930C24—C251.371 (5)
C11—C121.536 (4)C24—H240.930
C11—C161.548 (4)C25—H250.930
C10—Fe1—C642.1 (2)Fe1—C7—H7125.7
C10—Fe1—C4160.2 (3)C7—C8—C9111.2 (5)
C6—Fe1—C4153.2 (2)C7—C8—Fe171.7 (2)
C10—Fe1—C867.2 (2)C9—C8—Fe170.7 (2)
C6—Fe1—C864.65 (19)C7—C8—H8124.4
C4—Fe1—C8105.62 (18)C9—C8—H8124.4
C10—Fe1—C941.4 (2)Fe1—C8—H8124.8
C6—Fe1—C967.68 (18)C8—C9—C10107.5 (4)
C4—Fe1—C9121.6 (2)C8—C9—Fe170.5 (2)
C8—Fe1—C938.76 (19)C10—C9—Fe168.9 (2)
C10—Fe1—C3158.7 (3)C8—C9—H9126.3
C6—Fe1—C3120.5 (2)C10—C9—H9126.3
C4—Fe1—C340.90 (14)Fe1—C9—H9125.9
C8—Fe1—C3121.16 (19)C9—C10—C6103.0 (4)
C9—Fe1—C3156.3 (2)C9—C10—Fe169.7 (2)
C10—Fe1—C767.50 (19)C6—C10—Fe169.2 (2)
C6—Fe1—C738.27 (19)C9—C10—H10128.5
C4—Fe1—C7118.9 (2)C6—C10—H10128.5
C8—Fe1—C737.52 (17)Fe1—C10—H10124.4
C9—Fe1—C765.15 (18)C1—C11—C12110.2 (2)
C3—Fe1—C7106.38 (17)C1—C11—C16110.7 (2)
C10—Fe1—C5126.2 (2)C12—C11—C16107.7 (2)
C6—Fe1—C5165.9 (2)C1—C11—C17107.5 (2)
C4—Fe1—C540.56 (12)C12—C11—C17111.9 (2)
C8—Fe1—C5122.05 (18)C16—C11—C17108.8 (2)
C9—Fe1—C5109.02 (16)C13—C12—C11113.5 (2)
C3—Fe1—C568.32 (14)C13—C12—H12A108.9
C7—Fe1—C5154.2 (2)C11—C12—H12A108.9
C10—Fe1—C2125.3 (2)C13—C12—H12B108.9
C6—Fe1—C2110.72 (15)C11—C12—H12B108.9
C4—Fe1—C268.24 (13)H12A—C12—H12B107.7
C8—Fe1—C2157.83 (19)C14—C13—C12110.7 (3)
C9—Fe1—C2162.4 (2)C14—C13—H13A109.5
C3—Fe1—C240.38 (12)C12—C13—H13A109.5
C7—Fe1—C2125.25 (16)C14—C13—H13B109.5
C5—Fe1—C267.99 (12)C12—C13—H13B109.5
C10—Fe1—C1111.20 (15)H13A—C13—H13B108.1
C6—Fe1—C1129.33 (19)C15—C14—C13111.7 (3)
C4—Fe1—C168.47 (12)C15—C14—H14A109.3
C8—Fe1—C1159.04 (19)C13—C14—H14A109.3
C9—Fe1—C1125.96 (18)C15—C14—H14B109.3
C3—Fe1—C168.37 (12)C13—C14—H14B109.3
C7—Fe1—C1163.05 (18)H14A—C14—H14B107.9
C5—Fe1—C140.58 (11)C14—C15—C16111.9 (3)
C2—Fe1—C140.53 (11)C14—C15—H15A109.2
C5—C1—C2106.3 (3)C16—C15—H15A109.2
C5—C1—C11127.3 (3)C14—C15—H15B109.2
C2—C1—C11126.2 (3)C16—C15—H15B109.2
C5—C1—Fe168.32 (16)H15A—C15—H15B107.9
C2—C1—Fe168.69 (15)C15—C16—C11114.0 (3)
C11—C1—Fe1131.98 (19)C15—C16—H16A108.8
C3—C2—C1108.9 (3)C11—C16—H16A108.8
C3—C2—Fe169.12 (17)C15—C16—H16B108.8
C1—C2—Fe170.78 (15)C11—C16—H16B108.8
C3—C2—H2125.6H16A—C16—H16B107.7
C1—C2—H2125.6C21—C17—C18101.3 (2)
Fe1—C2—H2126.1C21—C17—C11118.6 (2)
C2—C3—C4108.0 (3)C18—C17—C11114.3 (2)
C2—C3—Fe170.50 (17)C21—C17—H17107.3
C4—C3—Fe169.37 (19)C18—C17—H17107.3
C2—C3—H3126.0C11—C17—H17107.3
C4—C3—H3126.0C19—C18—C17111.4 (3)
Fe1—C3—H3125.7C19—C18—H18124.3
C5—C4—C3107.9 (3)C17—C18—H18124.3
C5—C4—Fe170.25 (18)C18—C19—C20110.4 (3)
C3—C4—Fe169.74 (19)C18—C19—H19124.8
C5—C4—H4126.0C20—C19—H19124.8
C3—C4—H4126.0C25—C20—C21121.4 (3)
Fe1—C4—H4125.6C25—C20—C19130.8 (3)
C4—C5—C1108.9 (3)C21—C20—C19107.7 (3)
C4—C5—Fe169.19 (18)C22—C21—C20118.4 (3)
C1—C5—Fe171.10 (16)C22—C21—C17132.3 (3)
C4—C5—H5125.5C20—C21—C17109.2 (2)
C1—C5—H5125.5C23—C22—C21119.6 (3)
Fe1—C5—H5125.7C23—C22—H22120.2
C7—C6—C10108.0 (4)C21—C22—H22120.2
C7—C6—Fe171.4 (2)C24—C23—C22121.1 (3)
C10—C6—Fe168.7 (2)C24—C23—H23119.4
C7—C6—H6126.0C22—C23—H23119.4
C10—C6—H6126.0C25—C24—C23120.3 (3)
Fe1—C6—H6125.4C25—C24—H24119.8
C8—C7—C6110.3 (5)C23—C24—H24119.8
C8—C7—Fe170.8 (2)C24—C25—C20119.2 (3)
C6—C7—Fe170.3 (3)C24—C25—H25120.4
C8—C7—H7124.8C20—C25—H25120.4
C6—C7—H7124.8
C10—Fe1—C1—C5121.4 (3)C10—C6—C7—C80.4 (5)
C6—Fe1—C1—C5166.1 (3)Fe1—C6—C7—C859.6 (3)
C4—Fe1—C1—C537.36 (19)C10—C6—C7—Fe159.2 (3)
C8—Fe1—C1—C539.9 (5)C10—Fe1—C7—C881.5 (4)
C9—Fe1—C1—C576.8 (3)C6—Fe1—C7—C8121.0 (5)
C3—Fe1—C1—C581.5 (2)C4—Fe1—C7—C877.7 (4)
C7—Fe1—C1—C5156.4 (6)C9—Fe1—C7—C836.1 (3)
C2—Fe1—C1—C5118.6 (3)C3—Fe1—C7—C8120.2 (4)
C10—Fe1—C1—C2120.0 (3)C5—Fe1—C7—C846.2 (6)
C6—Fe1—C1—C275.3 (3)C2—Fe1—C7—C8160.3 (3)
C4—Fe1—C1—C281.3 (2)C1—Fe1—C7—C8170.5 (5)
C8—Fe1—C1—C2158.5 (5)C10—Fe1—C7—C639.6 (3)
C9—Fe1—C1—C2164.6 (3)C4—Fe1—C7—C6161.3 (3)
C3—Fe1—C1—C237.13 (19)C8—Fe1—C7—C6121.0 (5)
C7—Fe1—C1—C237.8 (6)C9—Fe1—C7—C684.9 (3)
C5—Fe1—C1—C2118.6 (3)C3—Fe1—C7—C6118.8 (3)
C10—Fe1—C1—C110.2 (4)C5—Fe1—C7—C6167.3 (3)
C6—Fe1—C1—C1144.9 (4)C2—Fe1—C7—C678.7 (3)
C4—Fe1—C1—C11158.6 (3)C1—Fe1—C7—C649.5 (7)
C8—Fe1—C1—C1181.4 (6)C6—C7—C8—C90.5 (5)
C9—Fe1—C1—C1144.4 (4)Fe1—C7—C8—C959.9 (3)
C3—Fe1—C1—C11157.3 (3)C6—C7—C8—Fe159.4 (3)
C7—Fe1—C1—C1182.4 (7)C10—Fe1—C8—C782.2 (4)
C5—Fe1—C1—C11121.2 (3)C6—Fe1—C8—C736.0 (3)
C2—Fe1—C1—C11120.1 (3)C4—Fe1—C8—C7117.3 (4)
C5—C1—C2—C30.6 (3)C9—Fe1—C8—C7121.3 (5)
C11—C1—C2—C3174.0 (3)C3—Fe1—C8—C775.7 (4)
Fe1—C1—C2—C358.8 (2)C5—Fe1—C8—C7158.2 (3)
C5—C1—C2—Fe158.19 (19)C2—Fe1—C8—C746.8 (6)
C11—C1—C2—Fe1127.2 (3)C1—Fe1—C8—C7172.3 (4)
C10—Fe1—C2—C3158.4 (3)C10—Fe1—C8—C939.1 (3)
C6—Fe1—C2—C3113.1 (3)C6—Fe1—C8—C985.4 (3)
C4—Fe1—C2—C338.1 (2)C4—Fe1—C8—C9121.4 (3)
C8—Fe1—C2—C339.7 (5)C3—Fe1—C8—C9162.9 (3)
C9—Fe1—C2—C3165.5 (5)C7—Fe1—C8—C9121.3 (5)
C7—Fe1—C2—C372.6 (3)C5—Fe1—C8—C980.5 (4)
C5—Fe1—C2—C382.0 (2)C2—Fe1—C8—C9168.1 (4)
C1—Fe1—C2—C3120.0 (3)C1—Fe1—C8—C951.0 (6)
C10—Fe1—C2—C181.6 (3)C7—C8—C9—C101.2 (5)
C6—Fe1—C2—C1126.9 (3)Fe1—C8—C9—C1059.2 (3)
C4—Fe1—C2—C181.88 (19)C7—C8—C9—Fe160.5 (3)
C8—Fe1—C2—C1159.7 (4)C10—Fe1—C9—C8118.5 (4)
C9—Fe1—C2—C145.6 (6)C6—Fe1—C9—C876.8 (3)
C3—Fe1—C2—C1120.0 (3)C4—Fe1—C9—C874.9 (3)
C7—Fe1—C2—C1167.4 (3)C3—Fe1—C9—C838.6 (6)
C5—Fe1—C2—C138.01 (17)C7—Fe1—C9—C835.0 (3)
C1—C2—C3—C40.3 (3)C5—Fe1—C9—C8117.9 (3)
Fe1—C2—C3—C459.5 (2)C2—Fe1—C9—C8165.1 (4)
C1—C2—C3—Fe159.8 (2)C1—Fe1—C9—C8159.9 (3)
C10—Fe1—C3—C255.8 (5)C6—Fe1—C9—C1041.7 (3)
C6—Fe1—C3—C286.6 (3)C4—Fe1—C9—C10166.6 (3)
C4—Fe1—C3—C2118.9 (3)C8—Fe1—C9—C10118.5 (4)
C8—Fe1—C3—C2163.6 (2)C3—Fe1—C9—C10157.2 (4)
C9—Fe1—C3—C2169.2 (4)C7—Fe1—C9—C1083.5 (3)
C7—Fe1—C3—C2125.7 (2)C5—Fe1—C9—C10123.6 (3)
C5—Fe1—C3—C281.1 (2)C2—Fe1—C9—C1046.6 (6)
C1—Fe1—C3—C237.27 (18)C1—Fe1—C9—C1081.6 (3)
C10—Fe1—C3—C4174.7 (4)C8—C9—C10—C61.4 (4)
C6—Fe1—C3—C4154.5 (3)Fe1—C9—C10—C661.7 (2)
C8—Fe1—C3—C477.4 (3)C8—C9—C10—Fe160.3 (3)
C9—Fe1—C3—C450.3 (5)C7—C6—C10—C91.1 (4)
C7—Fe1—C3—C4115.4 (3)Fe1—C6—C10—C962.0 (3)
C5—Fe1—C3—C437.84 (18)C7—C6—C10—Fe160.9 (3)
C2—Fe1—C3—C4118.9 (3)C6—Fe1—C10—C9113.4 (4)
C1—Fe1—C3—C481.6 (2)C4—Fe1—C10—C935.7 (6)
C2—C3—C4—C50.1 (4)C8—Fe1—C10—C936.6 (3)
Fe1—C3—C4—C560.1 (2)C3—Fe1—C10—C9154.6 (4)
C2—C3—C4—Fe160.2 (2)C7—Fe1—C10—C977.4 (3)
C10—Fe1—C4—C555.6 (5)C5—Fe1—C10—C977.3 (3)
C6—Fe1—C4—C5174.3 (3)C2—Fe1—C10—C9164.4 (3)
C8—Fe1—C4—C5121.4 (3)C1—Fe1—C10—C9120.8 (3)
C9—Fe1—C4—C582.5 (3)C4—Fe1—C10—C6149.1 (5)
C3—Fe1—C4—C5118.8 (3)C8—Fe1—C10—C676.8 (3)
C7—Fe1—C4—C5159.5 (2)C9—Fe1—C10—C6113.4 (4)
C2—Fe1—C4—C581.1 (2)C3—Fe1—C10—C641.1 (6)
C1—Fe1—C4—C537.38 (18)C7—Fe1—C10—C636.0 (3)
C10—Fe1—C4—C3174.3 (4)C5—Fe1—C10—C6169.2 (3)
C6—Fe1—C4—C355.5 (4)C2—Fe1—C10—C682.2 (3)
C8—Fe1—C4—C3119.9 (2)C1—Fe1—C10—C6125.8 (3)
C9—Fe1—C4—C3158.7 (2)C5—C1—C11—C12155.0 (3)
C7—Fe1—C4—C381.7 (2)C2—C1—C11—C1231.5 (4)
C5—Fe1—C4—C3118.8 (3)Fe1—C1—C11—C1261.5 (3)
C2—Fe1—C4—C337.63 (18)C5—C1—C11—C1635.9 (4)
C1—Fe1—C4—C381.39 (19)C2—C1—C11—C16150.6 (3)
C3—C4—C5—C10.4 (4)Fe1—C1—C11—C1657.6 (3)
Fe1—C4—C5—C160.2 (2)C5—C1—C11—C1782.8 (3)
C3—C4—C5—Fe159.8 (2)C2—C1—C11—C1790.7 (3)
C2—C1—C5—C40.6 (3)Fe1—C1—C11—C17176.3 (2)
C11—C1—C5—C4173.9 (3)C1—C11—C12—C13175.5 (2)
Fe1—C1—C5—C459.1 (2)C16—C11—C12—C1354.6 (3)
C2—C1—C5—Fe158.42 (19)C17—C11—C12—C1364.9 (3)
C11—C1—C5—Fe1127.0 (3)C11—C12—C13—C1457.0 (4)
C10—Fe1—C5—C4159.8 (3)C12—C13—C14—C1554.6 (4)
C6—Fe1—C5—C4169.3 (6)C13—C14—C15—C1653.4 (4)
C8—Fe1—C5—C475.9 (3)C14—C15—C16—C1153.8 (4)
C9—Fe1—C5—C4116.7 (3)C1—C11—C16—C15173.5 (3)
C3—Fe1—C5—C438.1 (2)C12—C11—C16—C1552.9 (3)
C7—Fe1—C5—C444.7 (4)C17—C11—C16—C1568.6 (3)
C2—Fe1—C5—C481.8 (2)C1—C11—C17—C2162.5 (3)
C1—Fe1—C5—C4119.8 (3)C12—C11—C17—C2158.7 (3)
C10—Fe1—C5—C180.5 (3)C16—C11—C17—C21177.6 (2)
C6—Fe1—C5—C149.6 (7)C1—C11—C17—C1856.9 (3)
C4—Fe1—C5—C1119.8 (3)C12—C11—C17—C18178.1 (2)
C8—Fe1—C5—C1164.3 (2)C16—C11—C17—C1863.0 (3)
C9—Fe1—C5—C1123.5 (3)C21—C17—C18—C190.0 (3)
C3—Fe1—C5—C181.62 (19)C11—C17—C18—C19128.7 (3)
C7—Fe1—C5—C1164.4 (3)C17—C18—C19—C200.0 (4)
C2—Fe1—C5—C137.97 (17)C18—C19—C20—C25177.3 (3)
C10—Fe1—C6—C7118.7 (4)C18—C19—C20—C210.0 (4)
C4—Fe1—C6—C738.6 (5)C25—C20—C21—C222.3 (4)
C8—Fe1—C6—C735.3 (3)C19—C20—C21—C22175.2 (3)
C9—Fe1—C6—C777.7 (3)C25—C20—C21—C17177.6 (3)
C3—Fe1—C6—C777.4 (3)C19—C20—C21—C170.0 (3)
C5—Fe1—C6—C7156.8 (6)C18—C17—C21—C22174.3 (3)
C2—Fe1—C6—C7121.1 (3)C11—C17—C21—C2259.8 (4)
C1—Fe1—C6—C7163.3 (2)C18—C17—C21—C200.0 (3)
C4—Fe1—C6—C10157.3 (4)C11—C17—C21—C20125.9 (3)
C8—Fe1—C6—C1083.4 (3)C20—C21—C22—C231.5 (4)
C9—Fe1—C6—C1041.0 (3)C17—C21—C22—C23175.5 (3)
C3—Fe1—C6—C10163.9 (3)C21—C22—C23—C240.4 (5)
C7—Fe1—C6—C10118.7 (4)C22—C23—C24—C251.7 (5)
C5—Fe1—C6—C1038.1 (8)C23—C24—C25—C200.9 (5)
C2—Fe1—C6—C10120.2 (3)C21—C20—C25—C241.1 (5)
C1—Fe1—C6—C1077.9 (3)C19—C20—C25—C24175.8 (3)

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C20H21)]
Mr382.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)13.232 (2), 11.6546 (18), 12.293 (2)
β (°) 92.881 (3)
V3)1893.4 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.80
Crystal size (mm)0.26 × 0.24 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.793, 0.866
No. of measured, independent and
observed [I > 2σ(I)] reflections
10458, 3887, 2407
Rint0.038
(sin θ/λ)max1)0.627
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.121, 1.01
No. of reflections3887
No. of parameters235
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.30

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Selected bond lengths (Å) top
Fe1—C12.074 (3)Fe1—C62.021 (4)
Fe1—C22.046 (3)Fe1—C72.035 (4)
Fe1—C32.028 (3)Fe1—C82.024 (4)
Fe1—C42.023 (3)Fe1—C92.026 (4)
Fe1—C52.037 (3)Fe1—C102.015 (4)
 

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